What to do this week before the crowds arrive
The ten days before Memorial Day are the last quiet stretch of the season. Here is how we would spend a weekday afternoon.
By Dotti Maguire
It is May 15. Memorial Day is ten days out. The whale watch boats are running, Hammond Castle has been open for two weeks, and the harbor smells like spring instead of winter. But the crowds are not here yet. The Rockport Farmers Market does not open until June 14. Cape Ann Museum is still closed for renovation until June 30. Saint Peter's Fiesta is six weeks away.
What this means in practice: you can park on Bearskin Neck on a Saturday afternoon. You can walk into a restaurant without a reservation. You can have a stretch of Halibut Point mostly to yourself.
If you are staying with us this week, here is how we would use the days.
A weekday morning
Start slow. The light at 7 a.m. this time of year is the good kind, low and clean, and the harbor is usually flat before the wind picks up around ten. Walk down to the water with a coffee. If you are in Gloucester, the HarborWalk runs from Stacy Boulevard east toward the State Fish Pier, and the granite benches with the inset story panels are worth stopping at. If you are in Rockport, take the loop out to the end of the breakwater off T-Wharf.
For breakfast, a few options that are reliably open this time of year: Sugar Magnolias on Main Street in Gloucester (now in their newer location), Brothers' Brew in Rockport for a donut and a coffee, or Pleasant Street Tea Co. if you want something quieter and you take your caffeine in leaves rather than beans.
A midday plan
This is the week to do the thing you keep meaning to do.
Hammond Castle. It reopened on Tuesday, April 28, 2026, and the first two weeks of any season are the best time to visit because the school groups have not started in earnest. The Great Hall is still the most theatrical room in any museum on the North Shore, and the cliff terrace looking out at Norman's Woe is doing exactly what John Hammond designed it to do.
Or a whale watch. Cape Ann Whale Watch began their 2026 season on Saturday, May 2, 2026, and 7 Seas is also running. The boats are not full this week. The whales are back on Stellwagen Bank, the captains will tell you what they are seeing, and you will be on the water with maybe a third of the people who will be on it in July.
Or Halibut Point. Bring a sandwich. The quarry is full, the ocean is right there, and the trails are dry now in a way they have not been since November.
A long walk
If the weather is good, Good Harbor before noon. The parking lot is not yet charging summer rates and the beach is essentially empty on a weekday. The sandbar to Salt Island shows up around low tide. You can walk it, poke around the island, and walk back. Just check a tide chart first. Getting stranded on Salt Island is a Gloucester rite of passage but it is not one we recommend.
For a less obvious walk: Dogtown. The interior of the cape, abandoned village, glacial boulders, and Roger Babson's Depression-era inscribed rocks ("USE YOUR HEAD," "NEVER TRY NEVER WIN"). Wear actual shoes. The trail markers are not great. Bring a map.
A working pier
Gloucester is a working fishing port. That has not changed in four hundred years and it has not changed this week. Walk along the inner harbor in the late afternoon when boats are coming back in. The lobster traps are stacked everywhere now because the season is ramping up. You can buy lobsters right off the boat at a few spots if you know where to look, and we are happy to point you to one if you email and ask.
Dinner this week
Reservations are easy. Use them anyway, but you do not need to think a week ahead.
For seafood with a view: 1606 at Beauport Hotel, or The Gloucester House on the harbor. For Italian, Tonno in Rockport or Causeway in Gloucester (Causeway does not take reservations and the wait can still be real, even now). For a quieter night, Franklin Cape Ann does a good bar seat. In Essex, The James Pub & Provisions has taken over the old Village Restaurant space and is worth the drive.
The point
Next weekend the season starts. Traffic on 128 northbound after 3 p.m. on Friday will look different. The line at Woodman's will get long. Parking will get harder.
This week, it is still ours. Use it.
